Despite being an evangelist for all things in the cloud, I’m actually a little reticent when trying out the latest web app. I find that my schedule is so busy that the time taken to learn an application tends to greatly outweigh any benefits that application can deliver. There are exceptions though…

TripIt is an online service that helps people organize all their travel plans—flights, hotels, rental cars, trains, cruises—no matter where they booked. To get started, travelers just forward their travel confirmation emails to [email protected] TripIt processes these emails and automatically creates a master itinerary with travel plans, daily weather, local maps, restaurant reservations, city guides and more. With TripIt, travelers can print, access and share their travel plans online, from a mobile device or even in their personal calendar.

It’s one of those services that is crazily simple, yet crazily useful. I travel both domestically and internationally a reasonable amount – this travel generally includes a bunch of flights, various hotel stays and the like. I’m also a bit of a fitness fan and I always like to know probably weather conditions for wherever I’m going to make the all important “gym or outside” decisions and the luggage requirements that stem from that.

TripIt really is the greatest thing in the world for what I do… I simply book my travel, hotels and other events and forward the confirmation emails onto TripIt. Nearly instantaneously, and in a lovely show of automagicalism, my personal calendar reflects all of my booking and I can click on individual event to see additional information (weather, sights to see, restaurants etc etc).

TripIt is a free service, in-part monetized by selling advertising to vendors who (forlornly in my case) hope that a showing next to an itinerary will cause me to change my plans and eat at the hideously expensive restaurant down in SoMA, San Francisco.

TripIt just launched a new, updated look. According to their press release they;

We added big share, print and edit buttons to the itinerary. Share your trips with friends and on social networks with one click. Plus, easy access to calendar sync and other handy tools.

The new “People” section shows you which of your TripIt connections will be close to you on your trip. It’s a great way to set up meetings, connect with friends and colleagues, and much more! Add connections to make the most of who’s close.

None of which makes the slightest bit of different to my particular use-case and none of which changes the bottom line fact that TripIt is free and that I have never and probably will never click (or even see for that matter) one of the ads they serve up to me.

But I still hope they solve the monetization conundrum – TripIt is altogether too good to lose.

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Ben Kepes is a technology evangelist, an investor, a commentator and a business adviser. His business interests include a diverse range of industries from manufacturing to property to technology. As a technology commentator he has a broad presence both in the traditional media and extensively online. Ben covers the convergence of technology, mobile, ubiquity and agility, all enabled by the Cloud. His areas of interest extend to enterprise software, software integration, financial/accounting software, platforms and infrastructure as well as articulating technology simply for everyday users.